Ultimate Guide to Planning a Multi-Destination Trip

The prospect of planning and booking a multi-destination trip can be quite daunting. Such trips are often complicated, the planning takes a lot of time, and you have to get everything to align. In this guide, I will give you my tips on what I do, when planning trips where I visit multiple destinations.

Why Book a Multi-Destination Trip?

You’ll get to visit more destinations

It should be cost effective vs flying back home each time between places

Research

The first steps to planning a multi-destination trip will be to do research and decide where you want to go. You’ll probably find that your initial plan will always change. Such as when I was planning my Asia trip I originally planned to start in Shanghai and my trip included Seoul and Tokyo, but I ended up not going to any of those destinations and went to completely different places and countries in Asia.

Decide Where You Want to Go

Have a big think about which regions you want to visit and whether you want your trip to be different destinations within a country, or if you’d prefer to visit multiple countries. It’s also worth checking in advance whether the country allows short visa-free stays, as this can make your planning and decisions a lot easier.

When I decide where I want to go I often get inspired by places I see on Instagram, and that can often lead to me booking a trip that includes destinations that I would never have thought to visit otherwise. You can also read blog posts such as top places to visit, such as my Europe post on cities that are good to visit: Ten Great Cities to Visit in Europe

Use Google Maps

One of the first things I do when planning a multi-destination trip, is to look on Google Maps to get a clear picture of where places are in relation to each other. This ensures I can book transportation in the most efficient way. Ie if you are visiting Europe and want to see France, Germany and Austria, then it probably wouldn’t make sense to visit France followed by Austria, then Germany, as Germany is in the middle.

Google Maps Screenshot – Route between three countries

Look at Connections Between Destinations

Google Flights – If I am travelling quite far and need to fly I will next look on Google Flights and see what the connections are like and whether the flights are affordable and not too long. Using Google Flights you can search using the Map view or just the Flights View. There are even options to filter on the number of stops, airline, price, flight times and various other options.

Screenshot of Google Flights Map View

Flixbus– If I am travelling in Europe I also look at the connection options on FlixBus. I have used Flixbus for quite a lot of trips and I find them cheap and provide a great quality service. When booking they have an awesome interactive map which helps you search for routes.

Flixbus Route Map

Planning

Now for the planning. Things may and do often change when planning, but you will probably have a good idea on the destinations you want to visit.

Create a Google Spreadsheet With Your Itinerary

Once I’ve established the route I want, I will then create a spreadsheet using Google Docs, such as below. This spreadsheet will include as many details as possible about the trip, such as:

Dates – Including the day of the week and the actual calendar date.

Location – The country and city, or place, that I am visiting. I also track how many days I will be in each place.

Booking Status – I update this as to whether accommodation and flights are booked.

Transfer details – How to get from the airport, bus, or train stop to the accommodation. By doing this research in advance it’ll make the start of your trip that much easier and enjoyable.

Hotel/accommodation details – Make a note of the dates, address, cost, contact number and free cancellation date, which is often possible through Booking.com.

Visa information – Whether or not a visa is required, and I will make a note if it’s been arranged.

Below is an example of my spreadsheet/itinerary for Asia. You could also add columns to track who is paying for what when you are travelling with someone else.

Click here for a blank version of the spreadsheet which you can download and use. You could then import this into Google Docs if you wanted to use it online, or open it using Microsoft Excel or similar program on your computer.

Using Google Spreadsheets to Plan a Trip

Keep it Affordable

When booking multi-destination trips you can keep it affordable by hopping between places in the most direct route. You can often do this on cheap flights, trains or buses.

For example, if you did a multi-destination trip in Europe which involves Berlin, Prague and Vienna, then you could use FlixBus or trains. The bus between these cities may cost around €19 between Berlin and Prague, and then around €15 between Prague and Vienna. So you see travelling like that is an incredibly cheap way to travel. If you prefer to travel by trains you could consider using Goeuro to plan your train travel.

Trains in India

Always Book Connecting Flights Through One Airline

If you need to book a flight that has a stopover, then try to book through one airline. That way it’s the airline’s responsibility to ensure you get on the connecting flights.

If you decide to book say one flight from London to Dubai, and then separately book another flight from Dubai to Singapore through completely different airlines, then if you have delays on the first flight and end up missing the second flight, you have less protection and may be responsible for buying an entirely new flight.

Flying

Be Wary of Delays and Cancellations

Flights can often be delayed, so you should always beware of potential delays, cancellations and other things that may come up. So when planning all your connections make sure you leave yourself ample time, so you don’t end up missing costly flights or having to rush around unnecessarily. In some destinations such as around Asia, I found there is less passenger protection than in Europe. In Europe, airlines may have to provide compensation for cancellations and delays. Head to europa.eu…passenger-rights to learn more about EU Flight Regulations.

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Accommodation

There are now so many accommodation options available from hotels, guesthouses, homestays, pet sitting, Airbnb, Couchsurfing and more.

Booking Hotels, Hostels and Guesthouses

I now book almost all my accommodation through Booking.com which I am a big fan of. Benefits to using them include:

Genius discounts for frequent bookers – After around 7 bookings you become a Genius member. This gives you extra discounts and other benefits.

Free cancellation – Many properties offer free cancellation up to a certain date, or sometimes the day before. This makes changing your plans a lot easier and cheaper.

Good filters – There are tons of filter options on the site. Such as price, accommodation type, free cancellation, review score, facilities, and many more.

Map view – If you would prefer there is a map view. I often use this to get a good idea of where the hotel is in the location.

Viewing bookings – In the view “bookings” you can easily see where you are staying from day to day in an easy to read format.

Pic: Booking.com Screenshot

There are a few things that do irritate me about Booking.com even though I use them a lot.

Unless you turn them off you will get lots of emails trying to make you book. I recommend turning these off in the settings.

They put unnecessary pressure on you, saying that x number of people are currently looking at the property. I find this super annoying and wish I could turn that off.

They sometimes show properties that no longer have rooms in a “Just Missed It” fashion! I personally don’t see the point in this other than to annoy me.

Despite these things, I still definitely rate them as one of the best providers. Do you know of any other hotel booking services that you recommend? Please let me know.

Booking using Airbnb

Another popular option for accommodation is Airbnb. These are private properties that people rent out and could be a house or flat. You can find properties where just a single room is available, or where the entire property is available. When checking in you will then arrange with the host a time, which can vary a lot as the host may have a normal 9-5 job. I have stayed in several properties with Airbnb and they were nice, clean and it was pretty easy to arrange everything.

Bedroom at a family house in India

House Swap, Pet Sitting and Other Options

Other accommodation options which may be good include house swapping, pet sitting or Couchsurfing. These aren’t options I’ve tried yet. If you have tried them please leave a comment as I’d love to know your thoughts.

Here are some websites that produce such services:

Home Exchange – This site is where you exchange your home with someone else, so you get to see their destination and they get to see yours and you both save money doing so.

Trusted Housesitters – Trustedhousesitters allows you to stay somewhere for free and you look after their pets in exchange.

Share your Itinerary with Friends and Family

Once you have everything planned you should share your itinerary with your friends and family. This is so that they know where you are throughout your trip. If you are using Google Docs to plan, and then you share the document, then any changes you make will automatically be updated and viewable in the shared document. If you don’t use Google Docs then forward any flights, accommodation and anything else important to them via email.